2,5-bis(trimethylsilyl)ferrocenecarboxaldehyde | 474669-50-6

• 英文名称: 2,5-bis(trimethylsilyl)ferrocenecarboxaldehyde
• CAS: 474669-50-6
• 化学式: C₁₇H₂₆FeOSi₂
• 分子量: 358.411
• InChiKey: DIGBNFOBIWBUBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2,5-bis(trimethylsilyl)ferrocenecarboxaldehyde 、 三丁基氯化锡 在 N-methylpiperazide 、 t-BuLi 作用下， 以 not given 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Selective Functionalization of Chiral Ferrocenyl Acetals. Easy Access to Various Tri- and Tetrasubstituted Ferrocenes with Controlled Geometry

  摘要：

  The lithiation of 2-substituted chiral dioxane 2, followed by electrophilic trapping of the lithiated intermediate, yields various 1,5-disubstitued acetals with good yields and excellent control of the geometry. These acetals can be easily hydrolyzed into various 1,5-disubstitued ferrocenecarboxaldehydes (in an enantiomerically pure form if the two substituents are different), which can be furthermore substituted on the other Cp ring to yield unprecedented 2,5, 1'-ferrocenecarboxaldehydes (in an enantiomerically pure form if they are chiral). The three substituents on ferrocenecarboxaldehyde can be different: this is, to the best of our knowledge, the first example of enantiomerically pure 1,2,3,1'-tetrasubstituted ferrocene with planar chirality only.

  DOI：

  10.1021/om020462g
• 作为产物：
  描述：

  (2S,4S)-4-(methoxymethyl)-2-[2,5-bis(trimethylsilyl)ferrocenyl]-1,3-dioxane 、 水 在 p-toluenesulfonic acid monohydrate 作用下， 以 二氯甲烷 、 水 为溶剂， 以90%的产率得到2,5-bis(trimethylsilyl)ferrocenecarboxaldehyde
  参考文献：
  名称：

  Selective Functionalization of Chiral Ferrocenyl Acetals. Easy Access to Various Tri- and Tetrasubstituted Ferrocenes with Controlled Geometry

  摘要：

  The lithiation of 2-substituted chiral dioxane 2, followed by electrophilic trapping of the lithiated intermediate, yields various 1,5-disubstitued acetals with good yields and excellent control of the geometry. These acetals can be easily hydrolyzed into various 1,5-disubstitued ferrocenecarboxaldehydes (in an enantiomerically pure form if the two substituents are different), which can be furthermore substituted on the other Cp ring to yield unprecedented 2,5, 1'-ferrocenecarboxaldehydes (in an enantiomerically pure form if they are chiral). The three substituents on ferrocenecarboxaldehyde can be different: this is, to the best of our knowledge, the first example of enantiomerically pure 1,2,3,1'-tetrasubstituted ferrocene with planar chirality only.

  DOI：

  10.1021/om020462g